EP0899013A1 - Neue Katalysatoren für die Umwandlungsreaktionen von organischen Verbindungen - Google Patents

Neue Katalysatoren für die Umwandlungsreaktionen von organischen Verbindungen Download PDF

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Publication number
EP0899013A1
EP0899013A1 EP98402060A EP98402060A EP0899013A1 EP 0899013 A1 EP0899013 A1 EP 0899013A1 EP 98402060 A EP98402060 A EP 98402060A EP 98402060 A EP98402060 A EP 98402060A EP 0899013 A1 EP0899013 A1 EP 0899013A1
Authority
EP
European Patent Office
Prior art keywords
catalyst
support
use according
particles
group viii
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP98402060A
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English (en)
French (fr)
Inventor
Blaise Didillon
Denis Uzio
Elisabeth Merlen
Thierry Pages
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IFP Energies Nouvelles IFPEN
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IFP Energies Nouvelles IFPEN
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Filing date
Publication date
Application filed by IFP Energies Nouvelles IFPEN filed Critical IFP Energies Nouvelles IFPEN
Publication of EP0899013A1 publication Critical patent/EP0899013A1/de
Withdrawn legal-status Critical Current

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/44—Palladium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
    • C10G45/32—Selective hydrogenation of the diolefin or acetylene compounds
    • C10G45/34—Selective hydrogenation of the diolefin or acetylene compounds characterised by the catalyst used
    • C10G45/40—Selective hydrogenation of the diolefin or acetylene compounds characterised by the catalyst used containing platinum group metals or compounds thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
    • B01J35/391—Physical properties of the active metal ingredient
    • B01J35/393—Metal or metal oxide crystallite size
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/61—Surface area
    • B01J35/612—Surface area less than 10 m2/g

Definitions

  • the present invention relates to a new catalyst comprising at least one support and at least one metal from group VIII of the classification periodic and characterized in that the metallic particles deposited on the support are not isolated from each other.
  • the supported metal catalysts consist of an active metal may for example be at least one noble metal such as platinum or palladium, deposited in the form of particles on a support.
  • the specific activity corresponds to the activity of the catalyst brought back to the number of metallic atoms accessible to the molecules to be transformed.
  • the number of accessible metallic atoms can be determined by techniques of chemisorption of probe molecules (oxygen, hydrogen, carbon monoxide) or from the particle size determined by electron microscopy. These different techniques are perfectly known to those skilled in the art.
  • the specific activity can also be called Number of rotation or “Turn over Frequency” (TOF).
  • TOF Number of rotation
  • the state of aggregation of the particles is characterized by an analysis by microscopy of the catalyst after reduction of the active phase to temperatures generally between 20 and 500 ° C.
  • analysis by microscopy shows that at least 50% of the particles and preferably at least 70% of the particles present on the support have a point of contact with at least one other particle.
  • the particles can be indifferently arranged in the form of clusters, agglomerates, rosaries or any other configuration for which preferably at least 50% of the particles and more advantageously at least 70% of the particles have at least one point of contact with at least one other particle.
  • the proportion of isolated particles is preferably less than 50% and more advantageously less than 30%.
  • the catalysts according to the present invention apply to the processes for hydrogenation of compounds comprising acetylenic, olefinic, ketone, aldehyde, acid, nitro functions and in particular to the processes for purifying olefinic cuts by selective hydrogenation.
  • the conditions generally used for this type of transformation are a temperature between 25 and 250 ° C, a pressure between 0.1 and 10 MPa and a hydrogen to charge ratio (vol / vol) between 1 and 150.
  • the charge is generally a cut resulting from a cracking process containing from 2 to 12 carbon atoms. It can also be a feedstock resulting from a process of dehydrogenation of ethylbenzene for the production of styrene. In this case, the phenylacetylene must be eliminated.
  • the space velocities are generally between 0.1 and 50 h -1 for the treatment of liquid charges and 500 to 30,000 h -1 for the treatment of gaseous charges.
  • the catalyst support according to the invention comprises at least one refractory oxide generally chosen from magnesium oxides, aluminum, silicon, zirconium, thorium, taken alone as a mixture between them or with oxides of other elements of the classification periodic. Coal, silico-aluminates, clays or any other compound that can serve as a support can also be used. This support can be used in powder form or after shaping; all shaping techniques is suitable for the invention.
  • the catalyst according to the invention also contains a group VIII metal of the periodic table.
  • This metal is preferably platinum, palladium or nickel when we dedicate the catalyst to the transformation of acetylenic or diene compounds.
  • ruthenium and rhodium when the catalyst is dedicated to the transformation of functions organic materials containing a heteroatom, such as oxygen or nitrogen.
  • the metal is introduced so as to obtain particles dispersed on a support such that at least 50% of the particles and preferably at least 70% of the particles have at least one point of contact between them.
  • a particularly suitable preparation technique is the impregnation of a solution containing oxide particles or metal to file in suspension.
  • the solvent can be water or a solvent organic.
  • the solution may contain a limited concentration of complexing agent making it possible to stabilize it, the complexing agent however not essential.
  • Another preparation technique is to impregnate a solution aqueous of a precursor of the metal to be deposited, this solution having characteristics (pH, ionic strength, salt concentration) allowing reach the stability limit of the metal precursor.
  • aqueous solutions of salts such as hexahydroxyplatinic acid and palladium nitrate. These examples are not limiting and should not limit the scope of the invention.
  • the catalyst After depositing the catalytic element (s) by impregnating the solutions, the catalyst is generally dried at 120 ° C, possibly calcined at temperatures generally between 120 ° C and 500 ° C and reduced to temperatures between room temperature and 500 ° C.
  • the group VIII metal content of the catalyst according to the invention is generally between 0.01 and 50% by weight. This content is adapted depending on the intended application.
  • the catalyst can also contain other elements such as example an alkali metal, an alkaline earth metal, a metalloid, such as sulfur.
  • Catalyst A is prepared from an alumina with a specific surface of 9 m 2 / g and a pore volume of 0.6 ml / g.
  • This support is in the form of 3 mm diameter balls.
  • This support is impregnated with a bis-acetylacetonate solution of palladium diluted in toluene. After impregnation, the support is dried then calcined at 300 ° C and reduced to 750 ° C.
  • the final palladium content is 0.3% by weight. Analysis by microscopy of this catalyst shows that the particles have a size 6.5 nm average. These particles are isolated on the support. The catalyst is therefore not in accordance with the invention.
  • the proportion of palladium accessible to molecules is measured by chemisorption of CO at temperature ambient. This proportion is 18%.
  • Catalyst B is prepared from the support described in the example 1. This support is impregnated with a palladium nitrate solution at pH 1.8. The volume of solution used is 0.6 ml per gram of support to to impregnate, to permeate.
  • the catalyst is dried at 120 ° C. and calcined at 450 ° C and reduced to 150 ° C.
  • the final catalyst contains 0.3% by weight of palladium.
  • Catalyst B is therefore in accordance with the invention.
  • the proportion of palladium accessible to molecules is measured by CO chemisorption at room temperature. This proportion is 16%.
  • Catalyst C is prepared under the conditions of Example 2 but using a solution of palladium nitrate diluted in nitric acid to pH 0.8.
  • the final catalyst contains 0.3% by weight of palladium.
  • a catalyst D is prepared under the conditions of Example 3 but the support has, in this case, a specific surface of 40 m 2 / g.
  • Catalyst D is therefore in accordance with the invention.
  • the proportion of palladium accessible to molecules is measured by CO chemisorption at room temperature. This proportion is 20%.
  • Catalyst E is prepared under the conditions of Example 4 except for the catalyst reduction temperature which is brought to 600 ° C at instead of 150 ° C.
  • Catalyst E is not therefore not in accordance with the invention.
  • the proportion of palladium accessible to molecules is measured by CO chemisorption at room temperature. This proportion is 18%.
  • the specific activity corresponds to the activity of the catalyst reduced to the amount of palladium accessible to the molecules.
  • Catalyst % accessible metal Particle size nm
  • Hydrogenating activity molecular weight of a metal
  • Specific activity molecular weight of a metal
  • the catalysts according the invention have a hydrogenating activity and an activity specific to at least twice as much as that of "comparative" catalysts.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
EP98402060A 1997-08-29 1998-08-14 Neue Katalysatoren für die Umwandlungsreaktionen von organischen Verbindungen Withdrawn EP0899013A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9710879A FR2767722B1 (fr) 1997-08-29 1997-08-29 Nouveau catalyseur utilisable dans les reactions de transformation de composes organiques
FR9710879 1997-08-29

Publications (1)

Publication Number Publication Date
EP0899013A1 true EP0899013A1 (de) 1999-03-03

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EP98402060A Withdrawn EP0899013A1 (de) 1997-08-29 1998-08-14 Neue Katalysatoren für die Umwandlungsreaktionen von organischen Verbindungen

Country Status (4)

Country Link
US (1) US6288295B1 (de)
EP (1) EP0899013A1 (de)
JP (1) JPH11226398A (de)
FR (1) FR2767722B1 (de)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1048346A1 (de) * 1999-04-29 2000-11-02 Institut Francais Du Petrole Katalysator mit schwach gedispergiertem Edelmetal und seine Verwendung für die Umwandlung von Kohlenwasserstoffeneinsätzen
FR2805542A1 (fr) * 2000-02-24 2001-08-31 Inst Francais Du Petrole Procede flexible de production de bases huiles et de distillats par une conversion-hydroisomerisation sur un catalyseur faiblement disperse suivie d'un deparaffinage catalytique
WO2008145387A2 (de) * 2007-05-31 2008-12-04 Süd-Chemie AG Katalysator zur selektiven hydrierung acetylenischer kohlenwasserstoffe und verfahren zu seiner herstellung
US8466082B2 (en) 2007-05-31 2013-06-18 Sued-Chemie Ip Gmbh & Co. Kg PD/AU shell catalyst containing HFO2, processes for the preparation and use thereof
US8586780B2 (en) 2007-05-31 2013-11-19 Sued-Chemie Ip Gmbh & Co. Kg Doped Pd/Au shell catalyst, method for producing the same and use thereof
US8927452B2 (en) 2007-05-31 2015-01-06 Sud-Chemie Ag Method for producing a shell catalyst and corresponding shell catalyst
US9617187B2 (en) 2008-11-30 2017-04-11 Sud-Chemie Ag Catalyst support, process for its preparation and use
US10150099B2 (en) 2007-05-31 2018-12-11 Alfred Hagemeyer Zirconium oxide-doped catalyst support, method for producing the same and catalyst containing a zirconium oxide-doped catalyst support

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL1009014C2 (nl) * 1998-04-28 1999-10-29 Dsm Nv Werkwijze voor de hydrogenering van fenylacetyleen in een styreenbevattend medium met behulp van een katalysator.
FR2796312B1 (fr) * 1999-07-16 2001-09-07 Atofina Catalyseur metallique supporte, sa preparation et ses applications dans la fabrication directe du peroxyde d'hydrogene
US20020009414A1 (en) * 1999-10-25 2002-01-24 Moser William R. Method of preparing compounds using cavitation and compounds formed therefrom
US20070066480A1 (en) * 1999-10-25 2007-03-22 Moser William R Method of preparing compounds using cavitation and compounds formed therefrom
US7521392B1 (en) * 2004-11-19 2009-04-21 Nanostellar, Inc. Supported catalysts having platinum particles
DE102007025444A1 (de) * 2007-05-31 2008-12-11 Süd-Chemie AG VAM-Schalenkatalysator, Verfahren zu dessen Herstellung sowie dessen Verwendung
RU2532924C1 (ru) * 2013-07-10 2014-11-20 Общество с ограниченной ответственностью "Газохим Техно" Катализатор окислительной конверсии углеводородных газов с получением оксида углерода и водорода
RU2552639C1 (ru) * 2013-11-19 2015-06-10 Общество с ограниченной ответственностью "Газохим Техно" Способ приготовления оксидно-полиметаллических катализаторов на основе жаропрочных сплавов для парциального окисления углеводородов в синтез-газ
US9790435B2 (en) * 2014-06-20 2017-10-17 Wayne State University Green diesel production from hydrothermal catalytic decarboxylation on a supported Pd—Co catalyst
WO2019022887A1 (en) * 2017-07-28 2019-01-31 Rohm And Haas Company HETEROGENEOUS CATALYST

Citations (4)

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Publication number Priority date Publication date Assignee Title
EP0488514A1 (de) * 1990-11-28 1992-06-03 Ford Motor Company Limited Verfahren zur Herstellung eines Katalysators für Kraftwagenabgase
EP0549543A2 (de) * 1991-12-04 1993-06-30 Tanaka Kikinzoku Kogyo K.K. Verfahren zur Herstellung eines hochdisperse Metallteilchen enthaltenden Trägerkatalysators
EP0580560A1 (de) * 1992-07-06 1994-01-26 Tanaka Kikinzoku Kogyo Kabushiki Kaisha Verfahren zur Herstellung eines hochdispersen Metallteilchen enthaltenden Trägerkatalysators
FR2707526A1 (fr) * 1993-07-12 1995-01-20 Cee Catalyseur supporté et procédé de préparation.

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US5105032A (en) * 1990-10-04 1992-04-14 The Dow Chemical Company Vapor phase hydrogenation of carbon tetrachloride
CA2099194A1 (en) * 1992-07-08 1994-01-09 Gustavo Larsen Sulfur tolerant bimetallic zeolitic reforming catalysts
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DE4323981C1 (de) * 1993-07-16 1995-03-09 Hoechst Ag Palladium und Kalium sowie Cadmium, Barium oder Gold enthaltender Schalenkatalysator, Verfahren zu dessen Herstellung sowie dessen Verwendung zur Herstellung von Vinylacetat
US5719097A (en) * 1993-07-22 1998-02-17 Chang; Clarence D. Catalyst comprising a modified solid oxide
JPH0910594A (ja) * 1995-04-28 1997-01-14 Mazda Motor Corp 排気ガス浄化用触媒
US5707921A (en) * 1995-09-15 1998-01-13 Phillips Petroleum Company Method of preparing isomerization catalyst composition
DE19645047A1 (de) * 1996-10-31 1998-05-07 Basf Ag Katalysatoren für die Aminierung von Alkylenoxiden, Alkoholen, Aldehyden und Ketonen
US5928983A (en) 1997-07-11 1999-07-27 Exxon Research And Engineering Co Process for the preparation of high activity carbon monoxide hydrogenation catalysts and the catalyst compositions
JPH11114419A (ja) * 1997-10-13 1999-04-27 Mitsui Mining & Smelting Co Ltd 一酸化炭素除去用触媒及びフィルター
DE19753464A1 (de) * 1997-12-02 1999-06-10 Basf Ag Palladium-Cluster und ihre Verwendung als Katalysatoren

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0488514A1 (de) * 1990-11-28 1992-06-03 Ford Motor Company Limited Verfahren zur Herstellung eines Katalysators für Kraftwagenabgase
EP0549543A2 (de) * 1991-12-04 1993-06-30 Tanaka Kikinzoku Kogyo K.K. Verfahren zur Herstellung eines hochdisperse Metallteilchen enthaltenden Trägerkatalysators
EP0580560A1 (de) * 1992-07-06 1994-01-26 Tanaka Kikinzoku Kogyo Kabushiki Kaisha Verfahren zur Herstellung eines hochdispersen Metallteilchen enthaltenden Trägerkatalysators
FR2707526A1 (fr) * 1993-07-12 1995-01-20 Cee Catalyseur supporté et procédé de préparation.

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1048346A1 (de) * 1999-04-29 2000-11-02 Institut Francais Du Petrole Katalysator mit schwach gedispergiertem Edelmetal und seine Verwendung für die Umwandlung von Kohlenwasserstoffeneinsätzen
FR2792851A1 (fr) * 1999-04-29 2000-11-03 Inst Francais Du Petrole Catalyseur a base de metal noble faiblement disperse et son utilisation pour la conversion de charges hydrocarbonees
US6660897B1 (en) 1999-04-29 2003-12-09 Institut Francais Du Petrole Catalyst based on a noble metal with low dispersion, and its use in converting hydrocarbon feeds
KR100766344B1 (ko) * 1999-04-29 2007-10-15 아이에프피 분산도가 낮은 귀금속계 촉매 및 탄화수소 공급원료의전환 반응에서의 이의 용도
CZ302024B6 (cs) * 1999-04-29 2010-09-08 Institut Français du Pétrole Katalyzátor obsahující alespon jeden vzácný kov a zpusob konverze uhlovodíkových surovin
FR2805542A1 (fr) * 2000-02-24 2001-08-31 Inst Francais Du Petrole Procede flexible de production de bases huiles et de distillats par une conversion-hydroisomerisation sur un catalyseur faiblement disperse suivie d'un deparaffinage catalytique
WO2008145387A3 (de) * 2007-05-31 2009-03-12 Sued Chemie Ag Katalysator zur selektiven hydrierung acetylenischer kohlenwasserstoffe und verfahren zu seiner herstellung
WO2008145387A2 (de) * 2007-05-31 2008-12-04 Süd-Chemie AG Katalysator zur selektiven hydrierung acetylenischer kohlenwasserstoffe und verfahren zu seiner herstellung
US8466082B2 (en) 2007-05-31 2013-06-18 Sued-Chemie Ip Gmbh & Co. Kg PD/AU shell catalyst containing HFO2, processes for the preparation and use thereof
US8586780B2 (en) 2007-05-31 2013-11-19 Sued-Chemie Ip Gmbh & Co. Kg Doped Pd/Au shell catalyst, method for producing the same and use thereof
US8927452B2 (en) 2007-05-31 2015-01-06 Sud-Chemie Ag Method for producing a shell catalyst and corresponding shell catalyst
US10150099B2 (en) 2007-05-31 2018-12-11 Alfred Hagemeyer Zirconium oxide-doped catalyst support, method for producing the same and catalyst containing a zirconium oxide-doped catalyst support
US9617187B2 (en) 2008-11-30 2017-04-11 Sud-Chemie Ag Catalyst support, process for its preparation and use

Also Published As

Publication number Publication date
JPH11226398A (ja) 1999-08-24
FR2767722B1 (fr) 1999-12-31
US6288295B1 (en) 2001-09-11
FR2767722A1 (fr) 1999-03-05

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